New Efficient Synthesis of 2,3,5-Trisubstituted Pyrimidin-4(3H)-ones from Baylis-Hillman Adducts

被引:12
作者
Zhong, Ying [1 ]
Wu, Lei [1 ]
Ding, Ming-Wu [1 ]
机构
[1] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China
来源
SYNTHESIS-STUTTGART | 2012年 / 44卷 / 19期
基金
中国国家自然科学基金;
关键词
azides; heterocycles; cyclizations; Wittig reactions; amines; alcohols; phenols; DERIVATIVES; ANTAGONISTS; CONSTRUCTION;
D O I
10.1055/s-0032-1317034
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Azides obtained from Baylis-Hillman adducts were treated with triphenylphosphine to give the corresponding iminophosphoranes that underwent aza-Wittig reactions with aryl isocyanates and then reacted with amines, alcohol, or phenols in the presence of catalytic amounts of sodium alkoxide or potassium carbonate to give the corresponding 2,3,5-trisubstituted pyrimidin-4(3H)-ones directly in good yields.
引用
收藏
页码:3085 / 3089
页数:5
相关论文
共 27 条
[21]   Synthesis of allylic thiocyanates and novel 1,3-thiazin-4-ones from 2-(bromomethyl)alkenoates and S-nucleophiles in aqueous medium [J].
Sa, Marcus M. ;
Fernandes, Luciano ;
Ferreira, Misael ;
Bortoluzzi, Adailton J. .
TETRAHEDRON LETTERS, 2008, 49 (07) :1228-1232
[22]  
Sá MM, 2003, J BRAZIL CHEM SOC, V14, P1005
[23]   Advances in the Baylis-Hillman reaction-assisted synthesis of cyclic frameworks [J].
Singh, Vijay ;
Batra, Sanjay .
TETRAHEDRON, 2008, 64 (20) :4511-4574
[24]   Nucleophilic displacement by azide and cyanide on Baylis-Hillman acetates in water [J].
Yadav, JS ;
Gupta, MK ;
Pandey, SK ;
Reddy, BVS ;
Sarma, AVS .
TETRAHEDRON LETTERS, 2005, 46 (16) :2761-2763
[25]   Synthesis and biological evaluation of novel 5-alkyl-2-arylthio-6-((3,4-dihydroquinolin-1(2H)-yl)methyl)pyrimidin-4(3H)-ones as potent non-nucleoside HIV-1 reverse transcriptase inhibitors [J].
Zhang, Jing ;
Zhan, Peng ;
Wu, Jingde ;
Li, Zhenyu ;
Jiang, Yan ;
Ge, Weiying ;
Pannecouque, Christophe ;
De Clercq, Erik ;
Liu, Xinyong .
BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (14) :4366-4376
[26]   Design and Synthesis of Pyrimidinone and Pyrimidinedione Inhibitors of Dipeptidyl Peptidase IV [J].
Zhang, Zhiyuan ;
Wallace, Michael B. ;
Feng, Jun ;
Stafford, Jeffrey A. ;
Skene, Robert J. ;
Shi, Lihong ;
Lee, Bumsup ;
Aertgeerts, Kathleen ;
Jennings, Andy ;
Xu, Rongda ;
Kassel, Daniel B. ;
Kaldor, Stephen W. ;
Navre, Marc ;
Webb, David R. ;
Gwaltney, Stephen L., II .
JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (02) :510-524
[27]   Base-catalyzed, efficient synthesis of 5-substituted 3,6-dihydro-7H-1,2,3-triazolo[4,5-d]pyrimidin-7-ones [J].
Zhao, JF ;
Xie, C ;
Ding, MW ;
He, HW .
SYNTHESIS-STUTTGART, 2005, (15) :2544-2548